1. Field of the Invention
The present invention relates to a camphor-derived β-amino alcohol compound, a method for manufacturing the same and asymmetric addition of organozinc to aldehydes using the same and, more particularly, to a easily prepared camphor-derived β-amino alcohol compound, a method for manufacturing the same and asymmetric addition of organozinc to aldehydes using the same.
2. Description of Related Art
Optically active alcohols play an important role in the synthesis of natural products, biologically active components, such as Orphenadrine, Neobenodine, Carbinoxamine, Efavirenz Fostriencin and Camptothecin. In particular, it has become increasingly clear that enantiomerically pure drugs have distinct biological activities, and thereby optically active alcohols may be critical intermediates for synthesis of new drugs.
The production of enantiomerically pure material has historically been achieved in one of two ways: the use of enantiomerically pure starting materials derived from natural sources (so-called chiral pool); and the resolution of racemic mixtures by classical techniques. However, the chiral pool is limited to compounds found in nature, so only certain structures and configurations are readily available. Regarding resolution of racemates, it may be inconvenient and time-consuming since the use of resolving agents is required.
Accordingly, asymmetric synthetic methods utilizing highly efficient chiral catalysts and auxiliaries have attracted the attention of synthetic organic chemists. Among the methods available for the synthesis of chiral alcohols, the enantioselective addition of organozincs to carbonyl compounds in the presence of chiral substances as catalysts shows the advantages of wide functional group tolerance, mild reaction conditions, and the use of low-toxic zinc metal. Regarding chiral substances, camphor and its derivatives are not only good chiral auxiliaries in asymmetric synthesis, but also useful chiral scaffolds for asymmetric catalysts. Chiral β-amino alcohol A (DAIB) shows impressive results in catalytic organozinc addition reactions, while β-amino alcohol B is inferior in catalyzing the ethylation reaction (23% ee).
